HCID 10702957, compound → HCID 10584033, compound
Reaction equation
[OH:1][C@@H:2]([P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9])[CH:3]=[C:4]([CH3:6])[CH3:5]>CO.[Pd]>[OH:1][C@@H:2]([P:7](=[O:12])([O:8][CH3:9])[O:10][CH3:11])[CH2:3][CH:4]([CH3:5])[CH3:6]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Dimethyl (S)-1-hydroxy-3-methyl-2-butenylphosphonate obtained in Example 31 (68% e.e., 54 mg) was dissolved in 10 ml of methanol, and 10% Pd/C (16 mg) was added thereto. The mixture was stirred at room temperature for 3 hours under hydrogen atmosphere. The reaction mixture was filtered through Celite and the filter cake was washed with ethyl acetate. The solvent was distilled under reduced pressure and the residue was purified by flash column chromatography (acetone/hexane=1/4, on SiO2) to obtain dimethyl (S)-1-hydroxy-3-methylbutylphosphonate as a final product in a yield of 98%. This compound is known to be useful as a raw material for medicines and the like. The chemical reaction in this Reference Example is shown in chemical formula 49.
Workup
- filtrationThe reaction mixture was filtered through Celite
- washthe filter cake was washed with ethyl acetate
- distillationThe solvent was distilled under reduced pressure
- customthe residue was purified by flash column chromatography (acetone/hexane=1/4, on SiO2)
Sources & evidence
- ORD record
- ord-a44adf988d6e46908e4f09b209e6a504
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05847186
Reaction notes
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